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South West England
Gloucestershire
Forest Of Dean
Tidenham

Chepstow Castle to Wyndcliff Wood — Wye Valley Way

Routes
Hiking trails & Routes
South West England
Gloucestershire
Forest Of Dean
Tidenham

Chepstow Castle to Wyndcliff Wood — Wye Valley Way

Moderate

4.6

(29)

168

hikers

Chepstow Castle to Wyndcliff Wood — Wye Valley Way

04:31

15.8km

370m

Hiking

Embark on a moderate hike along the Chepstow Castle to Wyndcliff Wood section of the Wye Valley Way, covering 9.8 miles (15.8 km) with an elevation gain of 1215 feet (370 metres). This route typically takes about 4 hours and 30 minutes to complete. You will traverse dense woodlands, featuring…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

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1

196 m

Chepstow Castle

Highlight • Viewpoint

Standing proudly on a limestone cliff above the River Wye, Chepstow Castle is a magnificent fortress with a history that stretches back nearly 1,000 years. Founded in 1067 by Earl …

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2

1.64 km

View of Chepstow Castle and the River Wye

Highlight • River

The views across the Wye at Chepstow Castle perched on its lofty craggy perch is super good from here. The Wye looks a bit murky but that is to be expected so close to the sea.

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3

3.89 km

View of the River Wye and the cave entrance in the Wye Valley National Landscape

Highlight • Cave

In 1975 the Wye Valley Walk opened with a 14 miles (23 km) stretch between St. Arvans and Monmouth. Further stretches were added, leading to it becoming a 34-mile (55 …

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4

3.99 km

Otter Hole Cave

Highlight • Natural Monument

Otter Hole / Otter Cave is known as one of the best "decorated" caves in the UK. Access is restricted to protect the rare formations inside. The cave also floods, …

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5

4.08 km

Giant's Cave, Wye Valley

Highlight • Cave

There are a couple of caves in this area. The first (coming from Chepstow) is very shallow and raided above the path.

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6

5.76 km

View from Eagles Nest

Highlight • Trail

Eagles Nest is situated at the top of a steep, wooded limestone cliff and as the highest point on the Monmouthshire bank of the Wye, at 770 foot (235 m). …

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7

7.04 km

Wyndcliff Wood

Highlight • Forest

8

7.87 km

9

12.9 km

Piercefield House Ruins

Highlight • Monument

A nice opportunity for someone into real estate development - Piercefield House awaits your attention.

A once-fine Georgian mansion, commissioned in 1785, it was sold to the Racecourse in 1925, abandoned and gradually became derelict.

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B

15.8 km

End point

Parking

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Way Types & Surfaces

Way Types

8.82 km

2.94 km

1.96 km

1.66 km

440 m

Surfaces

11.7 km

1.62 km

1.62 km

798 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

Powered by Foreca

Thursday 7 May

17°C

7°C

49 %

Additional weather tips

Max wind speed: 12.0 km/h

to get more detailed weather forecasts along your route

This route was planned by komoot.

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